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Spring/Summer 2019: Confidence, Unbidden

Mike Berry ’92 has been on top of the dot-com boom, but he’s also been bankrupt and unemployed. 

He dropped out of law school, but he’s also spent the past 15 years leading marketing programs for Apple, eBay, and PayPal. Now Berry is head of marketing technology at Shutterfly, a company responsible for 75 million gigabytes of data. If anyone knows second chances, it’s Mike Berry. WM asked him to shed some light on the dizzying highs and nauseating lows. 

The craziest professional decision I ever made was… 

To ask my mom for $72,000 to start my own company. 

When my dad passed away, I dropped out of law school. I had been volunteering at a tiny local magazine and the founder offered me 49 percent ownership if I stayed and worked there full time. I agreed and we turned it into a Web site, a rare thing in 1994. The site ended up winning some awards and we got a call one day from the largest radio station there in Sacramento to build their Web site for $25K. A couple months later we had several projects running, had hired several people, and I decided we needed to move to a real office and upgrade hardware. So, I called my mom and committed myself to running a Web site-development company. 

We ended up hiring nearly 20 people, building more than 100 Web sites for companies such as Intel, Peet’s Coffee, Duraflame, and Sutter Health. But we were so inexperienced that we didn’t handle client relationships well—“You need us to add another 15 pages to your Web site for free to keep you happy? Of course!”—and we had overhired. After nearly four and a half years, we went bankrupt. 

A hard lesson, but a great real-life MBA. 

My day isn’t complete without… 

A cup of iced caramel macchiato from Starbucks. Usually a venti with four shots. I think I have had one almost every day for the last 12 years. 

My dad drank 25 cups of coffee a day (his doctor said he was an experiment in over-caffeination) but died of a brain tumor when he was 53. I avoided coffee until I started working at PayPal where 70-hour weeks were the norm.

The best lesson I learned when I was unemployed was…

Network, network, network. 

After a couple of months of not finding a job, it can be easy to wallow in self-pity, start sleeping in, and become a recluse. You start to think that all the jobs are gone. 

I almost moved to try to find some somewhere else. But then I thought about John D. Rockefeller and how, after interviewing for every job opening in Cleveland, he went back and interviewed for them all over again. I did the same. Eventually, through a friend I had stayed in contact with, I was able to get a contract job at Business Objects. Since then my career has been stable.

My favorite guilty pleasure is…

Speed chess. I play almost every day. It’s one of the few things that allows me to completely forget about everything else. And the games are short—I can stop quickly to help my kids with their homework or discuss something with my wife.

Although…there have been nights where I have played 10 or more games in a row and maybe not gotten all the sleep I wanted.

I define success as…

Being useful. There is always something else that needs to be done.

My children have taught me…

To be honest. 

It is hard to admit that you don’t have all the answers, that you did not make the right choices, that you are human. But I think this is very important to your children; they need to know that they do not have to be perfect; that it is okay if they make mistakes, if they don’t get straight A’s, if they disagree with me. That life isn’t easy; it takes work. 

I find it hard to let this happen—I want everything to be easy and fun and rewarding for them. But they need to learn this themselves. I hope I can be a valuable guide.

When I can’t fall asleep, I…

Read or watch a documentary. 

Failure is…

When you don’t learn. 

I failed out of law school, started a company that went bankrupt, had to find a job at age 29 with “just” a bachelor’s degree (in philosophy of all things!) and then again at age 32. If I’d known that before my Wabash graduation, I would have seen my future as a failure. 

But those years I learned some of my most important lessons: that law simply wasn’t for me, that I do not memorize and follow; I engage, I envision, I lead. 

I learned how to manage people, teams. I learned accounting on the spot. I learned how to deal with strong personalities. 

I learned how to persevere. So many things in my first two decades were easy for me—I simply did not struggle until I was 24. But then I failed. And I learned. And I failed, and I learned. And, thanks to that painful education, my life has gotten pretty good. 

I would rather be stuck on an elevator for an entire day than…

Do many of the things my wonderful wife does. 

She is the one who makes sure we eat food other than pizza and peanut butter. She is the one who makes sure everyone gets to school on time. She makes sure that summer camps are aligned, that rides to and fro are organized. She ensures our vacations are amazing, that the house is clean, that life appears to be well-oiled. Her hard work, her grit, is what allows me to pursue a career, the kids to pursue their favorite activities, to excel at school, and to develop skills. 

She is the single best thing that has ever happened to me.

The biggest lesson I learned at Wabash was…


I remember when it started. I was sitting in Cultures & Traditions and realized I had an opinion about Chinua Achebe’s book Things Fall Apart. And I spoke it, unbidden. Then I had another one and another and I engaged in conversation with my classmates and with Professor Helman. And I enjoyed it! I started working on points to talk about for every C&T class, thought about my reasons and supporting points. I started doing the same thing in all my other classes. By my junior year I felt confident talking, arguing, conversing in every class I was taking in every subject we covered. 

By the end of Wabash I realized I was smart, I could succeed, and if I put my mind to it, I could do just about anything. That foundation of confidence got me through my challenges and drove me to my successes. 

—Questions by Christina Egbert